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Technical method for synthesizing beta p-hydroxy phenethyl alcohol

A technology for p-hydroxyphenethyl alcohol and synthesis process, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of long synthesis process route, poor process practicability, low production efficiency, etc., and achieves synthesis process route The effect of short, low production cost and high production efficiency

Inactive Publication Date: 2007-02-21
SHENYANG LIGONG UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0020] The purpose of the present invention is to provide a short synthetic process route, mild reaction conditions, high production efficiency and technical problems such as poor process practicability, long synthetic process route and low production efficiency in the synthesis of existing β-p-hydroxyphenethyl alcohol. The synthetic process method of β-hydroxyphenylethanol with low production cost has broad application prospects in industrial production, and makes the source of raw materials adopted widely, and the yield of phenyl acetate can reach 93%.

Method used

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  • Technical method for synthesizing beta p-hydroxy phenethyl alcohol
  • Technical method for synthesizing beta p-hydroxy phenethyl alcohol
  • Technical method for synthesizing beta p-hydroxy phenethyl alcohol

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Embodiment 1

[0034] (1) Esterification process: Take 47g (0.5mol) of phenol, 53mL (0.75mol) of acetic anhydride, add it to a 250mL three-necked flask with a reflux device, control the reaction temperature at 140±5°C, and react for 3.5 hours. The reaction is essentially complete. The obtained product is washed with water, then washed with sodium hydride, then washed with water, and then dried with anhydrous calcium chloride, the material after suction filtration is distilled, and the fraction at 190-200 ° C is collected to obtain phenyl acetate. The yield is was 90.8%.

[0035] (2) Alkylation process: get 13.6g (0.1mol) of phenyl acetate, the product of esterification process, 20mL (0.2mol) of 1,2-dichloroethane, and 0.5g phosphoric acid catalyst, add 70mLN , in a three-necked flask of N-dimethylformamide, keeping the reaction temperature at 100±5° C., a mixture of acetic acid-(4-β-haloethyl)phenyl esters was obtained after 6 hours. Then add 2 times of benzene to the mixture, wash with 10...

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Abstract

This invention discloses a method for synthesizing beta-p-hydroxyphenylethanol from phenol and acetic anhydride by esterification, halogen-alkylation and hydrolysis. Since the O atom on phenolic hydroxyl has a high electronegativity, it is easily subjected to alkylation reaction. To avoid the reaction, esterification is employed to preotect the O atom and phenyl acetate. Then 1,2-dihaloethylene is added on the benzene ring of phenyl acetate to obtain (4-beta-haloethyl)phenyl acetate. The protection groups are removed by hydrolysis to obtain beta-p-hydroxyphenylethanol. The method has such advantages as short synthesis route, mild reaction conditions, high efficiency, high yield (up to 93%), and abundant raw material resources.

Description

technical field [0001] The invention belongs to fine chemical synthesis technology, in particular to a process for preparing β-p-hydroxyphenethyl alcohol. Background technique [0002] β-Hydroxyphenethyl alcohol is an inhibitor of active oxides. It can inhibit the damage of peroxides to DNA, reduce the oxidation in bone marrow cells, and protect the production of red blood cells in bone marrow. β-Hydroxyphenethyl alcohol is also an important pharmaceutical intermediate, which can be used to synthesize many useful drugs, such as: Metoprolol (Metoprolol), also known as Metoprolol, is used for the treatment of hypertension, angina pectoris, Arrhythmia and myocardial infarction can also be used to treat hyperthyroidism and migraine; Betaxolol, also known as Betaxolol, can treat high blood pressure and open-angle glaucoma; maltine, an active ingredient of barley malt , can digest and neutralize food accumulation, not thinking about eating, abdominal distension and breast swellin...

Claims

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Application Information

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IPC IPC(8): C07C37/11C07C39/11
Inventor 李勇贺燕蔡广乐左继成倪君印郝仪
Owner SHENYANG LIGONG UNIV
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